本文選題：螺吡喃 + Cu~(2+)��； 參考：《遵義醫(yī)學(xué)院》2017年碩士論文

【摘要】：目的:構(gòu)建新的含螺吡喃環(huán)小分子化合物并探尋其分子識(shí)別性能和抗腫瘤活性。方法:以吲哚啉為原料,將其分別與2,6-二甲酰基-4-甲基苯酚、2,6-二甲�；�-4-叔丁基苯酚縮合反應(yīng)得到含螺吡喃環(huán)的中間體L1和L2;再將螺吡喃中間體L1與氮芥衍生物(N,N-二氯乙基-對(duì)苯二胺)縮合反應(yīng)得含氮芥的螺吡喃環(huán)小分子化合物L(fēng)3;對(duì)比化合物以費(fèi)舍爾氏醛與氮芥衍生物(N,N-二氯乙基-對(duì)苯二胺)縮合得到含氮芥的小分子化合物L(fēng)4。利用1H NMR,13C NMR,FT-IR,質(zhì)譜等分析技術(shù)進(jìn)行其結(jié)構(gòu)的表征。并應(yīng)用熒光分光光度計(jì)和紫外-可見分光光度計(jì)考察了L1和L2的識(shí)別性能;采用MTT法考察了L3和L4對(duì)腫瘤細(xì)胞的抗腫瘤活性。結(jié)果:成功合成并表征了L1,L2,L3和L4。經(jīng)研究發(fā)現(xiàn):中間體L1和L2在無水乙醇與Tris-HCl(1/1,v/v,pH=7.40)的混合溶劑中能特異選擇性識(shí)別Cu~(2+)和水合肼,且可實(shí)現(xiàn)對(duì)Cu~(2+)的裸眼比率識(shí)別。制成負(fù)載有L1和L2的試紙條能實(shí)現(xiàn)裸眼識(shí)別檢測(cè)水樣中μmol/L級(jí)的Cu~(2+),制備負(fù)載有L1和L2的TLC板及試紙片能實(shí)現(xiàn)在365 nm紫外燈下對(duì)液體和氣體水合肼的裸眼識(shí)別。L1和L2可應(yīng)用于水樣和藥物中Cu~(2+)或水合肼測(cè)定的回收率分別在83.5%~111.0%、72.6%~111.0%之間,相對(duì)標(biāo)準(zhǔn)偏差(RSD%)分別小于4.0%和3.0%。L2可應(yīng)用于活細(xì)胞中水合肼的成像;抗腫瘤化合物L(fēng)3和L4對(duì)A549和HepG2兩種細(xì)胞都具有一定的細(xì)胞毒性,且L3對(duì)A549的細(xì)胞毒性優(yōu)于順鉑,其抑制率IC50是順鉑的3.5倍。結(jié)論:L1和L2可作為高選擇性識(shí)別Cu~(2+)和水合肼的化學(xué)傳感器;L3可作為抗A549腫瘤細(xì)胞的潛在先導(dǎo)化合物。含螺吡喃結(jié)構(gòu)的小分子在多功能識(shí)別性能以及作為抗腫瘤先導(dǎo)化合物研究中具有其潛在的應(yīng)用前景。
[Abstract]:Aim: to construct a new small molecular compound containing spiropyran ring and to explore its molecular recognition and anti-tumor activity. Methods: indoline was used as raw material. The intermediate L1 and L _ 2 containing spiropyran ring were obtained by condensation reaction of 2-butadiyl -4-methylphenol and 2-diformyl-6-diformyl-4-tert Ding Ji phenol, respectively, and then the intermediate L1 and nitrogen mustard derivative (N-N-dichloroethyl-p-phenylenediamine) were synthesized. The spiropyran ring small molecular compound L3 containing nitrogen mustard was synthesized by condensation reaction, and the small molecule compound L4 containing nitrogen mustard was synthesized by condensation of Fischer aldehyde with nitrogen mustard derivative N (N-dichloroethyl-p-phenylenediamine). Its structure was characterized by 1H-NMR-13C NMR-FT-IRand mass spectrometry. The recognition properties of L1 and L2 were investigated by fluorescence spectrophotometer and UV-Vis spectrophotometer, and the antitumor activity of L3 and L4 on tumor cells was investigated by MTT method. Results: L1, L2, L3 and L4 were successfully synthesized and characterized. It has been found that the intermediates L1 and L2 can specifically identify Cu~(2 and hydrazine hydrate in the mixture of anhydrous ethanol and Tris-HCln (1 / 1 / 1 / v / v pH = 7.40), and can realize the naked eye ratio recognition of Cu~(2). The test strips loaded with L1 and L2 can be used to detect the 渭 mol/L grade Cu~(2 in water samples. The TLC plates loaded with L1 and L2 and the test sheets can recognize liquid and gas hydrazine hydrate by naked eyes under 365nm UV lamp. The recoveries of L2 for the determination of Cu~(2 in water samples and drugs) or hydrazine hydrate were 83.5% and 111.0%, respectively. The relative standard deviation (RSD) is less than 4.0% and 3.0%.L2 can be used in the imaging of hydrazine hydrate in living cells, the antitumor compounds L3 and L4 are cytotoxic to both A549 and HepG2 cells, and the cytotoxicity of L3 to A549 is better than that of cisplatin. The inhibition rate of IC50 was 3.5 times higher than that of cisplatin. Conclusion 1: L1 and L2 can be used as chemical sensors for highly selective recognition of Cu~(2) and hydrazine hydrate as potential lead compounds for anti-A549 tumor cells. Small molecules with spiropyran structure have potential applications in the study of multifunctional recognition and antitumor precursor compounds.
【學(xué)位授予單位】：遵義醫(yī)學(xué)院
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：R914;R96

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本文編號(hào)：1879006